Formaldehyde → Glyphosate

HRID 464570Notes

Reaction equation

HRID 464570 reaction equation
S(=[N:4][CH2:5][C:6]([OH:8])=[O:7])(=O)=O.[CH3:9][O-].[Na+].C=O.C[O:15][P:16]([O:19]C)[O:17]C>CO>[CH2:5]([NH:4][CH2:9][P:16]([OH:19])([OH:17])=[O:15])[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8472Trimethyl phosphiteHCID 10942334Sodium Methoxide2×HCID 17806686HCID 17806686, compound

Product 1

HCID 3496Glyphosate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-sulfonylglycine (5 grams, 0.032 mole), prepared in the prior example, was suspended in methanol (50 mls) and sodium methoxide (25% sodium hydroxide in methanol) was added to adjust the pH of the suspension to 8-9. Paraformaldehyde (1 gram, 0.033 mole) and trimethylphosphite (3.8 mls, 0.032 mole) were added to the suspension and the resulting reaction mixture was then refluxed. The pH was adjusted with sodium methoxide solution from time to time to maintain it between 8 and 9. After 5 hours, the solids present in the reaction mixture were separated and the filtrate was evaporated. The resulting residue was refluxed with concentrated HCl (25 mls). After 3 hours, the solvent was removed to obtain the product glyphosate. This product was isolated and the structure confirmed by H and 31P NMR spectroscopy.

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas then refluxed
  3. temperatureto maintain it between 8 and 9
  4. customthe solids present in the reaction mixture were separated
  5. customthe filtrate was evaporated
  6. temperatureThe resulting residue was refluxed with concentrated HCl (25 mls)
  7. waitAfter 3 hours
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-e3ce22e5f21a427fa2ee9350543afa0c
Source dataset
uspto-grants-1985_10
Patent number
US04548758

Reaction notes

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